{"id":25772,"date":"2025-05-15T13:48:35","date_gmt":"2025-05-15T12:48:35","guid":{"rendered":"https:\/\/wpcms.chambers.com\/?post_type=legal-trends&#038;p=25772"},"modified":"2025-05-15T13:48:37","modified_gmt":"2025-05-15T12:48:37","slug":"irs-section-269-tax-avoidance","status":"publish","type":"legal-trends","link":"https:\/\/wpcms.chambers.com\/legal-trends\/irs-section-269-tax-avoidance\/","title":{"rendered":"Back from the Shadows: Section 269 and the IRS\u2019s Renewed Crackdown on Tax Avoidance"},"content":{"rendered":"\n<p>In the latest episode of Chambers Expert Focus Weil Tax Insight series, Devon Bodoh, head of international tax at Weil Gotshal &amp; Manges, and tax partner Greg Featherman delve into the renewed relevance of Section 269 of the Internal Revenue Code \u2013 an infrequently used anti-abuse rule that the IRS is now actively applying in response to perceived tax avoidance schemes.<\/p>\n\n\n\n\n\n<p>Historically underutilised, Section 269 prohibits a company from acquiring control of another when the primary purpose is to obtain tax benefits \u2013 such as deductions, credits or deferrals \u2013 that would not otherwise be available. Although it has existed for decades, it had largely faded from the spotlight until recently, with the last major academic discussion of the statute dating back to the 1970s and early 1980s.<\/p>\n\n\n\n<iframe src=\"https:\/\/share.zencast.fm\/embed\/episode\/57e4c05a-872f-460d-ac04-2fa8870f294f\" width=\"100%\" height=\"190\" frameborder=\"0\" scrolling=\"no\" seamless=\"true\" style=\"width: 100vw; max-width:100%; height:190px;\"><\/iframe>\n\n\n\n<p>The catalyst for its resurgence was a Chief Counsel Advice (CCA) issued by the IRS, which involved a US taxpayer using check-the-box planning and a fiscal year-end change to defer income under the GILTI rules introduced by the 2017 tax reform. Specifically, a foreign subsidiary elected to be treated as a corporation and adopted a November 30th year-end, thereby enabling an 11-month window of tax deferral. The IRS ruled that this restructuring violated Section 269, as the principal purpose was deemed to be tax avoidance.<\/p>\n\n\n\n\n\n<p>Featherman and Bodoh outline the technical facts of the case, emphasising that while the strategy complied with the letter of existing rules, the IRS disqualified the benefits based on the substance-over-form principle enshrined in Section 269. The implications are significant: even standard tax elections and structuring techniques \u2013 previously seen as routine \u2013 may now trigger scrutiny.<\/p>\n\n\n\n<p>The podcast explores the broader implications, noting this move could cast a long shadow over common planning strategies, such as forming blocker corporations or utilising foreign entities for tax deferral. While the CCA is not binding precedent, it signals the IRS\u2019s willingness to apply general anti-abuse doctrines more aggressively, even in cases lacking clear statutory or regulatory anti-abuse provisions.<\/p>\n\n\n\n\n\n<p>Importantly, the partners express concern not just about IRS enforcement, but about auditors and attestation firms overreacting to this CCA. Bodoh notes that the vagueness of Section 269 creates room for overly conservative audit positions that could chill legitimate business transactions.<\/p>\n\n\n\n\n\n<p>Though the specific facts of the CCA are unusual, and may not be broadly applicable, it is clear that taxpayers and advisers must now account for Section 269 in structuring decisions.<\/p>\n\n\n\n\n\n\n","protected":false},"featured_media":0,"template":"","meta":[],"publication":[],"locations":[],"blocks":[{"blockName":"core\/paragraph","attrs":[],"innerBlocks":[],"innerHTML":"\n<p>In the latest episode of Chambers Expert Focus Weil Tax Insight series, Devon Bodoh, head of international tax at Weil Gotshal &amp; Manges, and tax partner Greg Featherman delve into the renewed relevance of Section 269 of the Internal Revenue Code \u2013 an infrequently used anti-abuse rule that the IRS is now actively applying in response to perceived tax avoidance schemes.<\/p>\n","innerContent":["\n<p>In the latest episode of Chambers Expert Focus Weil Tax Insight series, Devon Bodoh, head of international tax at Weil Gotshal &amp; Manges, and tax partner Greg Featherman delve into the renewed relevance of Section 269 of the Internal Revenue Code \u2013 an infrequently used anti-abuse rule that the IRS is now actively applying in response to perceived tax avoidance schemes.<\/p>\n"]},{"blockName":null,"attrs":[],"innerBlocks":[],"innerHTML":"\n\n","innerContent":["\n\n"]},{"blockName":"lazyblock\/chambers-media-list","attrs":{"media-list":"%5B%7B%22title%22:%22Devon%20Bodoh%22,%22buttonName%22:%22View%20profile%22,%22content%22:%22Ranked%20in%20Chambers%20USA:%20Tax%22,%22buttonUrl%22:%22https:\/\/chambers.com\/lawyer\/devon-bodoh-usa-5:1181981%22,%22image%22:%7B%22alt%22:%22Devon%20Bodoh,%20Weil,%20EF%20contributor%22,%22title%22:%22Devon%20Bodoh,%20Weil%22,%22caption%22:%22%22,%22description%22:%22%22,%22id%22:15388,%22link%22:%22https:\/\/wpcms.chambers.com\/legal-trends\/spin-off-taxation-in-the-usa\/devon-bodoh-circle\/%22,%22url%22:%22https:\/\/assets.chambers.com\/wp-content\/uploads\/2023\/04\/14120422\/Devon-Bodoh-circle.jpg%22,%22sizes%22:%7B%22thumbnail%22:%7B%22height%22:120,%22width%22:120,%22url%22:%22https:\/\/assets.chambers.com\/wp-content\/uploads\/2023\/04\/14120422\/Devon-Bodoh-circle-120x120.jpg%22,%22orientation%22:%22landscape%22%7D,%22medium%22:%7B%22height%22:300,%22width%22:300,%22url%22:%22https:\/\/assets.chambers.com\/wp-content\/uploads\/2023\/04\/14120422\/Devon-Bodoh-circle-300x300.jpg%22,%22orientation%22:%22landscape%22%7D,%22large%22:%7B%22height%22:1024,%22width%22:1024,%22url%22:%22https:\/\/assets.chambers.com\/wp-content\/uploads\/2023\/04\/14120422\/Devon-Bodoh-circle-1024x1024.jpg%22,%22orientation%22:%22landscape%22%7D,%22full%22:%7B%22url%22:%22https:\/\/assets.chambers.com\/wp-content\/uploads\/2023\/04\/14120422\/Devon-Bodoh-circle.jpg%22,%22height%22:1696,%22width%22:1696,%22orientation%22:%22landscape%22%7D%7D%7D%7D,%7B%22title%22:%22Greg%20Featherman%22,%22buttonName%22:%22View%20firm%20profile%22,%22buttonUrl%22:%22https:\/\/chambers.com\/law-firm\/weil-gotshal-manges-llp-global-2:3667%22,%22image%22:%7B%22alt%22:%22%22,%22title%22:%22Greg-Featherman-circ%22,%22caption%22:%22%22,%22description%22:%7B%22raw%22:%22%22,%22rendered%22:%22%3Cp%20class=%5C%22attachment%5C%22%3E%3Ca%20href='https:\/\/wpcms.chambers.com\/wp-content\/uploads\/2023\/11\/Greg-Featherman-circ.jpg'%3E%3Cimg%20width=%5C%22300%5C%22%20height=%5C%22300%5C%22%20src=%5C%22https:\/\/assets.chambers.com\/wp-content\/uploads\/2023\/11\/03120215\/Greg-Featherman-circ-300x300.jpg%5C%22%20class=%5C%22attachment-medium%20size-medium%5C%22%20alt=%5C%22%5C%22%20srcset=%5C%22https:\/\/assets.chambers.com\/wp-content\/uploads\/2023\/11\/03120215\/Greg-Featherman-circ-300x300.jpg%20300w,%20https:\/\/assets.chambers.com\/wp-content\/uploads\/2023\/11\/03120215\/Greg-Featherman-circ-120x120.jpg%20120w,%20https:\/\/wpcms.chambers.com\/wp-content\/uploads\/2023\/11\/Greg-Featherman-circ.jpg%20366w%5C%22%20sizes=%5C%22(max-width:%20300px)%20100vw,%20300px%5C%22%20\/%3E%3C\/a%3E%3C\/p%3E%5Cn%22%7D,%22id%22:18204,%22link%22:%22https:\/\/wpcms.chambers.com\/?attachment_id=18204%22,%22url%22:%22https:\/\/wpcms.chambers.com\/wp-content\/uploads\/2023\/11\/Greg-Featherman-circ.jpg%22,%22sizes%22:%22%22%7D%7D%5D","blockId":"ToK9S","blockUniqueClass":"lazyblock-chambers-media-list-ToK9S"},"innerBlocks":[],"innerHTML":"","innerContent":[]},{"blockName":null,"attrs":[],"innerBlocks":[],"innerHTML":"\n\n","innerContent":["\n\n"]},{"blockName":"core\/paragraph","attrs":[],"innerBlocks":[],"innerHTML":"\n<p>Historically underutilised, Section 269 prohibits a company from acquiring control of another when the primary purpose is to obtain tax benefits \u2013 such as deductions, credits or deferrals \u2013 that would not otherwise be available. Although it has existed for decades, it had largely faded from the spotlight until recently, with the last major academic discussion of the statute dating back to the 1970s and early 1980s.<\/p>\n","innerContent":["\n<p>Historically underutilised, Section 269 prohibits a company from acquiring control of another when the primary purpose is to obtain tax benefits \u2013 such as deductions, credits or deferrals \u2013 that would not otherwise be available. Although it has existed for decades, it had largely faded from the spotlight until recently, with the last major academic discussion of the statute dating back to the 1970s and early 1980s.<\/p>\n"]},{"blockName":null,"attrs":[],"innerBlocks":[],"innerHTML":"\n\n","innerContent":["\n\n"]},{"blockName":"core\/html","attrs":[],"innerBlocks":[],"innerHTML":"\n<iframe src=\"https:\/\/share.zencast.fm\/embed\/episode\/57e4c05a-872f-460d-ac04-2fa8870f294f\" width=\"100%\" height=\"190\" frameborder=\"0\" scrolling=\"no\" seamless=\"true\" style=\"width: 100vw; max-width:100%; height:190px;\"><\/iframe>\n","innerContent":["\n<iframe src=\"https:\/\/share.zencast.fm\/embed\/episode\/57e4c05a-872f-460d-ac04-2fa8870f294f\" width=\"100%\" height=\"190\" frameborder=\"0\" scrolling=\"no\" seamless=\"true\" style=\"width: 100vw; max-width:100%; height:190px;\"><\/iframe>\n"]},{"blockName":null,"attrs":[],"innerBlocks":[],"innerHTML":"\n\n","innerContent":["\n\n"]},{"blockName":"core\/paragraph","attrs":[],"innerBlocks":[],"innerHTML":"\n<p>The catalyst for its resurgence was a Chief Counsel Advice (CCA) issued by the IRS, which involved a US taxpayer using check-the-box planning and a fiscal year-end change to defer income under the GILTI rules introduced by the 2017 tax reform. Specifically, a foreign subsidiary elected to be treated as a corporation and adopted a November 30th year-end, thereby enabling an 11-month window of tax deferral. The IRS ruled that this restructuring violated Section 269, as the principal purpose was deemed to be tax avoidance.<\/p>\n","innerContent":["\n<p>The catalyst for its resurgence was a Chief Counsel Advice (CCA) issued by the IRS, which involved a US taxpayer using check-the-box planning and a fiscal year-end change to defer income under the GILTI rules introduced by the 2017 tax reform. Specifically, a foreign subsidiary elected to be treated as a corporation and adopted a November 30th year-end, thereby enabling an 11-month window of tax deferral. The IRS ruled that this restructuring violated Section 269, as the principal purpose was deemed to be tax avoidance.<\/p>\n"]},{"blockName":null,"attrs":[],"innerBlocks":[],"innerHTML":"\n\n","innerContent":["\n\n"]},{"blockName":"lazyblock\/chambers-quote","attrs":{"quote":"<p>\u201cThe IRS has sent us a signal that they will be applying Section 269 in an aggressive manner.\u201d<\/p>","blockId":"Z1Wsf5Q","blockUniqueClass":"lazyblock-chambers-quote-Z1Wsf5Q"},"innerBlocks":[],"innerHTML":"","innerContent":[]},{"blockName":null,"attrs":[],"innerBlocks":[],"innerHTML":"\n\n","innerContent":["\n\n"]},{"blockName":"core\/paragraph","attrs":[],"innerBlocks":[],"innerHTML":"\n<p>Featherman and Bodoh outline the technical facts of the case, emphasising that while the strategy complied with the letter of existing rules, the IRS disqualified the benefits based on the substance-over-form principle enshrined in Section 269. The implications are significant: even standard tax elections and structuring techniques \u2013 previously seen as routine \u2013 may now trigger scrutiny.<\/p>\n","innerContent":["\n<p>Featherman and Bodoh outline the technical facts of the case, emphasising that while the strategy complied with the letter of existing rules, the IRS disqualified the benefits based on the substance-over-form principle enshrined in Section 269. The implications are significant: even standard tax elections and structuring techniques \u2013 previously seen as routine \u2013 may now trigger scrutiny.<\/p>\n"]},{"blockName":null,"attrs":[],"innerBlocks":[],"innerHTML":"\n\n","innerContent":["\n\n"]},{"blockName":"core\/paragraph","attrs":[],"innerBlocks":[],"innerHTML":"\n<p>The podcast explores the broader implications, noting this move could cast a long shadow over common planning strategies, such as forming blocker corporations or utilising foreign entities for tax deferral. While the CCA is not binding precedent, it signals the IRS\u2019s willingness to apply general anti-abuse doctrines more aggressively, even in cases lacking clear statutory or regulatory anti-abuse provisions.<\/p>\n","innerContent":["\n<p>The podcast explores the broader implications, noting this move could cast a long shadow over common planning strategies, such as forming blocker corporations or utilising foreign entities for tax deferral. While the CCA is not binding precedent, it signals the IRS\u2019s willingness to apply general anti-abuse doctrines more aggressively, even in cases lacking clear statutory or regulatory anti-abuse provisions.<\/p>\n"]},{"blockName":null,"attrs":[],"innerBlocks":[],"innerHTML":"\n\n","innerContent":["\n\n"]},{"blockName":"lazyblock\/chambers-quote","attrs":{"quote":"<p>\u201cThis has a pretty big chilling effect\u2026 not because of the IRS, but because of how every audit firm may react.\u201d<\/p>","blockId":"Z1AYoS5","blockUniqueClass":"lazyblock-chambers-quote-Z1AYoS5"},"innerBlocks":[],"innerHTML":"","innerContent":[]},{"blockName":null,"attrs":[],"innerBlocks":[],"innerHTML":"\n\n","innerContent":["\n\n"]},{"blockName":"core\/paragraph","attrs":[],"innerBlocks":[],"innerHTML":"\n<p>Importantly, the partners express concern not just about IRS enforcement, but about auditors and attestation firms overreacting to this CCA. Bodoh notes that the vagueness of Section 269 creates room for overly conservative audit positions that could chill legitimate business transactions.<\/p>\n","innerContent":["\n<p>Importantly, the partners express concern not just about IRS enforcement, but about auditors and attestation firms overreacting to this CCA. Bodoh notes that the vagueness of Section 269 creates room for overly conservative audit positions that could chill legitimate business transactions.<\/p>\n"]},{"blockName":null,"attrs":[],"innerBlocks":[],"innerHTML":"\n\n","innerContent":["\n\n"]},{"blockName":"lazyblock\/chambers-quote","attrs":{"quote":"<p>\u201cAnti-abuse rules by their nature are easy for auditors to apply, because they are subjective.\u201d<\/p>","blockId":"2kj2uQ","blockUniqueClass":"lazyblock-chambers-quote-2kj2uQ"},"innerBlocks":[],"innerHTML":"","innerContent":[]},{"blockName":null,"attrs":[],"innerBlocks":[],"innerHTML":"\n\n","innerContent":["\n\n"]},{"blockName":"core\/paragraph","attrs":[],"innerBlocks":[],"innerHTML":"\n<p>Though the specific facts of the CCA are unusual, and may not be broadly applicable, it is clear that taxpayers and advisers must now account for Section 269 in structuring decisions.<\/p>\n","innerContent":["\n<p>Though the specific facts of the CCA are unusual, and may not be 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In Focus Newsletter","content":"Sign up for our newsletter and never miss out on thought leadership content from legal experts and the key stories driving the legal profession forward.","button-title":"Sign up here","button-url":"https:\/\/crm.chambers.com\/l\/854103\/2023-07-05\/h7hd2 ","blockId":"Z2emDOb","blockUniqueClass":"lazyblock-promo-block-Z2emDOb"},"innerBlocks":[],"innerHTML":"","innerContent":[]}],"new_scheduled_revision":null,"save_as_revision":null,"acf":{"sponsored_page":false,"media_type":"podcast","index_page":"","firm_page_url":"","social_sharing_post_options":{"alignment":"left","sticky":false},"title":"","sponsors_list":{"sponsors":false,"showhide_borders":false},"hero_title":"","hero_description":"","hero_content_color":"light","hero_enable_responsive_images":false,"hero_image":false,"hero_retina_image":false,"useful_links":false,"template":{"name":"text-rich-media","sticky_sidebar":false}},"yoast_head":"<!-- This site is optimized with the Yoast SEO Premium plugin 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